ArticleACS omega2020
2,6-Dicyano-4-pyrone as a Novel and Multifarious Building Block for the Synthesis of 2,6-Bis(hetaryl)-4-pyrones and 2,6-Bis(hetaryl)-4-pyridinols.
Article in ACS omega, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Catalyst-Free Gas-Phase Synthesis of Pyrones via Thermally Induced Aldol Condensation of Acetoacetate Derivatives Using GC-MS.ACS omega · 2026Article
- 2-(2-(Dimethylamino)vinyl)-4Molecules (Basel, Switzerland) · 2022Article
- 2-Aryl-6-Polyfluoroalkyl-4-Pyrones as Promising RMolecules (Basel, Switzerland) · 2021Article
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Authors and funding
4 authors.
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No grant is acknowledged in the PubMed record.
Abstract
In this work, a three-stage and easily scalable synthesis of 2,6-dicyano-4-pyrone (overall yield of 45%) as a new convenient building block has been developed from diethyl acetonedioxalate. It was shown that the transformation with hydroxylamine and [3 + 2]-cycloaddition, in contrast to the reactions with hydrazines, selectively proceed through the attack at the cyano groups without the pyrone ring-opening to give symmetrical and unsymmetrical pyrone-bearing heterocyclic triads containing 1,2,4- and 1,3,4-oxadiazoles as well as tetrazole moieties. The reaction of 2,6-bis(hetaryl)-4-pyrones with ammonia afforded 2,6-bis(hetaryl)pyridines in 63-87% yields. The 4-pyridone/4-pyridinol tautomerism of 2,6-bis(hetaryl)pyridinols and the influence of the nature of adjacent azolyl moieties on this equilibrium have been discussed.
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Registered trials
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